Phenyl 3-methylsulfonylphenylcarbamate → N-(4-(7-(Benzyloxy)-6-cyano-4-quinolyl)oxyphenyl)-N'-(3-(methylsulfonyl)phenyl)urea

HRID 853246Notes

Reaction equation

HRID 853246 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:29][S:30]([C:33]1[CH:34]=[C:35]([NH:39][C:40](=O)[O:41]C2C=CC=CC=2)[CH:36]=[CH:37][CH:38]=1)(=[O:32])=[O:31]>CS(C)=O.C(OCC)(=O)C>[CH2:20]([O:19][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:40]([NH:39][C:35]4[CH:36]=[CH:37][CH:38]=[C:33]([S:30]([CH3:29])(=[O:32])=[O:31])[CH:34]=4)=[O:41])=[CH:28][CH:27]=3)=[CH:8][CH:9]=[N:10]2)=[CH:15][C:14]=1[C:17]#[N:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 22936234Phenyl 3-methylsulfonylphenylcarbamateHCID 229368314-(4-Aminophenoxy)-7-(benzyloxy)-6-cyanoquinoline

Product 1

HCID 22936455N-(4-(7-(Benzyloxy)-6-cyano-4-quinolyl)oxyphenyl)-N'-(3-(methylsulfonyl)phenyl)ureaYield 100%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

After dissolving 4-(4-aminophenoxy)-7-(benzyloxy)-6-cyanoquinoline (919 mg, 2.5 mmol) in dimethylsulfoxide (10 ml), phenyl N-(3-(methylsulfonyl)phenyl)carbamate (801 mg, 2.75 mmol) was added and the mixture was heated at 85° C. for 2 hours. The reaction solution was diluted with ethyl acetate and then washed with IN aqueous sodium hydroxide (10 ml), water (20 ml×2) and saturated brine (10 ml) and dried over anhydrous sodium sulfate. After filtering off the drying agent, the filtrate was concentrated under reduced pressure and the residue was suspended in ethyl acetate (30 ml), after which hexane (30 ml) was added, sonication was performed and the precipitated crystals were filtered out and dried under reduced pressure to obtain the title compound (1.43 g, 2.5 mmol, quantitative) as light brown crystals.

Workup

  1. additionwas added
  2. washwashed with IN aqueous sodium hydroxide (10 ml), water (20 ml×2) and saturated brine (10 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtering off the drying agent
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionafter which hexane (30 ml) was added
  7. customsonication
  8. filtrationthe precipitated crystals were filtered out
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-7be062fca3a94d3db3365e270fe386c4
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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